Anthony Scaramucci - My Biggest Failure? Working For Donald Trump

Scaramucci’s 11-day tenure as the White House Communications Chief under President Donald Trump’s first term ended in a blaze of recrimination. Scaramucci was advised by a PR consultant to disappear for five years. He refused - and reinvented his career. Now, he is the co-host of the US version of The Rest is Politics podcast alongside British journalist Katty Kay. After Harvard Law School, he joined Goldman Sachs and built a career in finance, eventually founding the investment firm SkyBridge Capital. In this revealing conversation we discuss what working on Wall Street in the 80s was like, getting fired from Goldman Sachs, his failed first marriage, not being there for his son’s birth, getting fired from The White House and rebuilding his current marriage. His book, All the Wrong Moves, looks at how three catastrophic decisions and years of ‘sh*tshow politics’ led to Trump. IN THIS EPISODE: 00:00 Introduction montage 03:22 Learning optimism and pronoia 05:02 Self forgiveness after failure 06:40 Growing up and getting to Tufts 11:58 Why he wrote the book 14:03 Fired then rehired at Goldman 25:23 Money mindset and marriage cracks 30:48 Work Taxes Burnout 31:26 Marriage Neglect Regrets 34:07 Conflict Avoidance Trap 34:55 Affair Self Forgiveness 37:46 Fatherhood After Divorce 40:44 Trump Ego Decision 45:00 Firing from The Whitehouse 57:03 Rebuilding and Looking Ahead 💬 QUOTES TO REMEMBER: When bad things happen, take a step back, and get into a channel that is the adult channel. Act in a rational way. I trained my brain to be optimistic. If you’re not careful, wealth can make you very depressed and lonely. Trump's bullying reminded me of my dad… but I was better prepared for it. 🔗 LINKS + MENTIONS: Anthony’s book, All the Wrong Moves, is available to buy now: www.penguin.co.uk/books/476667/all-the-wrong-moves-by-scaramucci-anthony/9781847929235 Join the How To Fail community: www.howtofail.supportingcast.fm/#content Elizabeth’s Substack: www.theelizabethday.substack.com 📚 WANT MORE? Bernie Sanders - swap.fm/l/pH8V6cBejDnhH47ega6D Andy Burnham - swap.fm/l/IpwatiJ5cM1h0UfcyFiA 💌 LOVE THIS EPISODE? Subscribe on Spotify, Apple or wherever you get your podcasts Leave a 5⭐ review – it helps more people discover these stories 👋 Follow How To Fail & Elizabeth: Instagram: @elizabday TikTok: @howtofailpod Podcast Instagram: @howtofailpod Website: www.elizabethday.org Elizabeth and Anthony answer listener questions in our subscriber series, Failing with Friends. Join our community of subscribers here: https://lnk.to/7i0moR Have a failure you’re trying to work through for Elizabeth to discuss? Click here to get in touch: askhowtofail.com Production & Post Production Coordinator: Eric Ryan Engineer: Matias Torres Assistant Producer: Shania Manderson Senior Producer: Hannah Talbot Executive Producer: Alex Lawless How to Fail is an Elizabeth Day and Sony Music Entertainment Production. Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts To bring your brand to life in this podcast, email [email protected] Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I was in a pretty abusive domestic situation as a kid. I had done everything right to get the most coveted job, except I was not interested in the job and I sucked at the job. When you say eighties on Wall Street, and I got there in the late eighties, early nineties, I'm thinking cocaine and booze. But go ahead, let me take you through my day on the 31st of July, okay? I am fired from the White House. I have missed the birth of my son. My wife has filed for divorce on me. I am torched and excoriated by the late night comedians.

• 0:35Elizabeth Day?

  This episode of How to Fail is brought to you by Ala Lacto Free. Hello and welcome to How to Fail with me, Elizabeth Day. This is the podcast that believes failure is the shadow twin to success. Before we get into this episode, please do remember to like, follow and subscribe so that you never miss a single episode. Confession time. I have a tendency to postpone certain decisions for far longer than is sensible. Not the big life decisions, oddly enough, those I can usually handle. It's the smaller ones that somehow become disproportionately complicated. For me, rugs fall squarely into that category. I've known for a long time that a rug can completely change how a room feels, but I've

• 1:19Elizabeth Day?

  always found sizing for a space tricky. That's why Ernesta appealed to me. Ernesta makes designer quality rugs custom cut to the exact dimensions of your space. So instead of making do with something that's close enough, you're choosing something made specifically for your home. I also love the fact that you can order five oversized 12 by 12 samples for just $10 before committing and Ernesta's design team will help with sizing completely free of charge. Visit ernestacom and order five samples for only $10 and you'll get $50 towards any rug of your choice. That's ernestacom.

• 1:59Elizabeth Day?

  My guest today is a Lamborghini driving financier, author and broadcaster who describes himself as an epic failure. And it's true that Anthony Scaramucci has never hidden his missteps from public view. Quite the opposite, in fact. His 11 day tenure as the White House Communications Chief under President Donald Trump's first term ended in a blaze of recrimination. Scaramucci was advised by a PR consultant to disappear for five years. He refused and reinvented his career. Now he is perhaps best known in this country for being the co-host of the US version of The Rest Is Politics podcast alongside British journalist, Katie Kay.

• 2:42Elizabeth Day?

  As a podcaster, Scaramucci has attracted a legion of new fans, many of whom see him not only as the rare Republican voice of reason in an increasingly fractious political landscape, but also as the thinking woman's crumpet. Scaramucci's paternal grandfather emigrated to the United States from Umbria in Italy. He had a working class upbringing in Long Island. His father was a construction worker, his mother a makeup artist, and he was the first in his family to attend college, earning a BA in economics at Tufts University and later going on to study at Harvard Law School. From there, he joined Goldman Sachs and built a career in finance, eventually founding the investment firm, Skybridge Capital.

• 3:26Elizabeth Day?

  His new book, All the Wrong Moves, examines how three catastrophic decisions and, as he puts it, years of shit show politics led to Trump. Scaramucci is particularly well placed to tell the story, as he says, "I've gotten the living shit beaten out of me about three or four times and I've been humbled by life." Anthony Scaramucci, welcome to How to Fail.

• 3:49Speaker 00

  It was a pretty generous introduction.

• 3:52Elizabeth Day?

  I feel generous when I think of you.

• 3:54Speaker 00

  Well, thank you.

• 3:55Elizabeth Day?

  You've got me through some tough times, most notably the last US election.

• 3:59Speaker 00

  It's been a tough time. I mean, it's interesting, you know, it's a decade now where Trump has loomed over the political landscape. And weirdly, that four year interregnum period made him more malicious, more malevolent and sort of, he was like, hey, man, I didn't steal enough in the first term. He had four years to figure out how to steal more. So it's been difficult. I mean, and we got two plus years to go.

• 4:24Elizabeth Day?

  You strike me as someone who is innately optimistic about life. Would that be fair?

• 4:30Speaker 00

  I'm too short to see the glass anything other than half full. I mean, just so everybody knows, before this podcast started, they told me to sit up. So I was trying to sit up, but my, my legs are dangling like the Shrek from, you know, the first prince in the Shrek movie.

• 4:44Elizabeth Day?

  Not dangling, but are you innately optimistic? Were you born like that?

• 4:48Speaker 00

  No, very much so. No, no, I wasn't born like that. I think that's interesting. I, I come up from, I come from a family of blue collar pessimists. I find that like the neighborhood I grew up in, everybody, you know, everybody's decided that the universe is against them. And so you have to train yourself to think in the opposite direction. So actually, I'm 35 years old now, but I read a book called Learned Optimism when I was in my early twenties. It was written by a psychologist by the name of Martin Seligman. And I remember I was in school and I said, okay, this is the antithesis of the way my family thinks. I have to force myself to think in this optimistic way. And so I become an optimist through training, but I didn't start out as an optimist.

• 5:33Elizabeth Day?

  How interesting. And do you still have to practice it daily or does it just come naturally?

• 5:38Speaker 00

  Now I don't have to practice. In fact, I talk to younger people about the word pro noia. Do you know this word?

• 5:44Elizabeth Day?

  Is it the opposite of paranoia?

• 5:45Speaker 00

  It is. Yeah. P R O N O I A. You have to believe that about the universe. You have to believe that the universe is bending towards you in your life. When you do that, even when really bad things happen to you, you can see the bright side to it. Accepting failure, ladies and gentlemen.

• 6:02Elizabeth Day?

  Exactly.

• 6:03Speaker 00

  Yes, I mean, you know, it's fine.

• 6:04Elizabeth Day?

  Well, it's part of what I really like and admire about you is that you are so open about failures being learning opportunities.

• 6:11Speaker 00

  Yeah. I mean, well, listen, you, you have two choices when you fail. You can slink away and hide, you can pretend that it didn't happen, you could lack accountability, you can play the victim, you can blame others. I mean, I can give you the whole list of things that you can do, which is, I think, the greatness of your podcast, because I think what you're trying to tell people, and it's really good in the UK culture for people to feel this way, it's okay to fail. There's no shame in it. Where the shame comes in is if you're not honest with yourself, because what'll end up happening is you'll dig yourself a hole that you can't get out of. You know, imagine if I had failed from the White House and then just slinked away and then was dreaded by that for the rest of my life, you know?

• 6:55Speaker 00

  I mean, the coin of failure is tied to forgiveness. And so when you're flipping that coin and you see it land on failure, flip it over, you have to forgive your failures. If you don't do that, that's a, that's a mistake in life. Life's too short not to forgive your own failures.

• 7:14Elizabeth Day?

  That's so profound.

• 7:16Speaker 00

  You just need to think about it that way, though, you know? I remember, you know, we, you know, if you grow up Christian, I was raised as a Roman Catholic, they teach you about redemption and forgiveness, but how about forgiving yourself? I don't walk around with a millstone of regret on my neck every morning. I don't kick myself in the pants every morning and say, jeez, I made a terrible decision to go work for Donald Trump. Let me kick myself in the pants this morning. You know, you gotta let that go and you gotta focus on today and tomorrow.

• 7:42Elizabeth Day?

  Former classmates and teachers of yours remember you as being slick and popular. One former teacher was quoted in Vanity Fair saying, "He was always very political. He knew how to get things done with different groups. He was a very smooth character." Do you recognize that?

• 7:58Speaker 00

  I mean, that's probably the, I mean, listen, I was a little bit of a renegade and a rogue in, in high school. So one of my teachers said that I would try to put a, a gallon of water in a one quart bottle, which I guess he thought I only had one quart of capacity, but it meant I would try to do too much in my life, which I've certainly tried to do that. I would, I would say in response to that, because I did read that, I would say I was definitely a character in high school, but I was a wayward character. I was hang out, I was trying to socialize with women, I bought myself a used Camaro. I was sort of like an Italian Guido out cruising on Long Island.

• 8:41Speaker 00

  If we're really going to be honest, my, my role model was like Tony Manero from Saturday Night Live. How bad is that, right? I mean, I had the gold chains, I had my hair slicked back like John Travolta in the movie. I was believing too much of my own BS, you know? And I didn't get straightened out until my senior year in high school. I, when I look back on that, there was a gross period of immaturity, actually.

• 9:06Elizabeth Day?

  What straightened you out?

• 9:07Speaker 00

  You know, my parents actually, you know, my father was like, sort of like the strong, silent, working class type. I mean, he was strict disciplinarian. I mean, he used to beat the daylights out of us, but that was customary back in that day. But, but he was a loving guy and he wanted us to do well. He wanted us to go to college. He didn't have the money for the schools that I went to. And so I had gotten into Tufts University, which I don't know if it's a well-known school here in the United Kingdom, but it was a, you know, it's probably like a top 25 private school in the US. And I had gotten into the state school, which is a good school, but it was up in Binghamton, New York. It was sort of a remote area. Tufts is like right in Boston, next to Harvard University.

• 9:52Speaker 00

  And my guidance counselor went to see my father and my mother and Elizabeth, they were smoking cigarelos, just to set the scene for you. And we had this little tiny circular table, just right off the hallway kitchen. And my mother was pouring the espresso and it was coming out of the, this cast iron pot like motor oil. Okay, it's like eight o'clock at night. They're smoking cigarelos and drinking espresso that is like six times the gavination of anything you'd find at a Starbucks. I mean, these people, I don't know how their hearts didn't explode. And John Zanetti, in Italian, spoke to my, it was actually a dialect of Italian, southern, southern dialect. They were all from that area.

• 10:36Speaker 00

  And he, he told my father, you gotta have Anthony go to the private school, have him go to Tufts. My father thought it was spelled like T O U G H S. He literally had no clue. But the very next day, he told me he was cashing in his life insurance policy from his union and he gave me a $10,000 check. Probably two weeks later, he handed me the check and he said, okay, you're going to go to Tufts. I don't really have the money for it. I cashed in my life insurance, got the cash value for it to help you get started. And I think that scared me straight. I felt that the love to do that and then the sacrifice and then the pressure, I was like, okay, I don't want to let my dad down. I gotta make sure I, I study. So I like literally.

• 11:22Speaker 00

  Drop the Camaro. I bought myself a Nissan Sentra, which is like not a flashy car at all. And I went to school and I got very good grades at Tufts and good enough grades to get myself into Harvard Law School.

• 11:34Elizabeth Day?

  There could be no higher stakes in so many ways.

• 11:37Speaker 00

  Yeah, it was, it paid off for my old man. I used to always tease him. He passed away in 2023. I was like, you know, that $10,000 cashier's check from your life insurance paid off for you. I used to tease him.

• 11:47Elizabeth Day?

  2023. So did he see you launch this second half of your career as a podcaster?

• 11:54Speaker 00

  No.

• 11:54Elizabeth Day?

  No.

• 11:54Speaker 00

  No. So I started the podcast in April of 24, but you know, look, he, he got to see the ups and downs of my political career, the ups and downs of my Wall Street career. And you know, for my parents, if they remember, the bar was low. I mean, all they wanted us to do was go to college, you know? I mean, funny part about my mother is my mother wanted me to be a lawyer. So I went to Harvard Law School, but I never practiced law. And she used to lie to her blue collar friends in the neighborhoods. I was in Rosanna's Deli ordering myself like a, you know, big salami sandwich. And I'm standing there next to Mrs. Kazenza, who's my mother's best friend. And she's like, how is that, how is that law firm Goldman Sachs? How is that law firm? I'm like, what? She goes, your mother told

• 12:36Speaker 00

  me you're working as a lawyer at Goldman Sachs. I'm like, she did? She says, yes. I said, it's Mrs. Kazenza. It's great. And I'm like, I call my mother, I'm like, why are you lying to your friends? I'm embarrassed for you that you're this investment banker.

• 12:51Elizabeth Day?

  That's amazing.

• 12:51Speaker 00

  I don't even know what that is.

• 12:53Elizabeth Day?

  That's amazing.

• 12:54Speaker 00

  That's, you know, that was the neighborhood I grew up in. I mean, no one knew anything. They didn't know the difference between Goldman Sachs and you picked the law firm, you know?

• 13:01Elizabeth Day?

  Before we get on to your failures, tell me why you wanted to write this book?

• 13:05Speaker 00

  First thing that came to mind for this book, and I had the idea for it a few years ago, but there are so many people, like I travel the country, I do a lot of public speaking. This is even before the podcast. So, you know, from the notoriety of getting fired from the White House, like speeches, corporate speeches, how to build yourself back up. There was a lot of resilient speeches, different things like that. And when I would travel the country, I would be astonished at the following rhetorical question. How did we get here? What happened to this country where we have this morose tribalism? We have this anger-based populism? What actually happened to the country? And so this is a

• 13:49Speaker 00

  reflection on my 38-year Wall Street career. This is some input from my failure as a White House Communications Director from Donald Trump, but also my observation as a political fundraiser for three decades for the Republican Party. And then it's also a little bit about my upbringing, because I did grow up in a blue collar neighborhood where my, my parents had bought a house, thank God. They paid $16,000 for it in 1962. And we had a good upbringing. I would never dishonor my dad or my father's work ethic by telling you I grew up poor, did not grow up poor. But, you know, we had a tight budget and things were, we had to be disciplined about what we were buying and things like that. So I have that perspective.

• 14:32Speaker 00

  And then I was able to go to Goldman Sachs and build some measure of wealth. And then I created a couple of successful hedge fund businesses. And so, you know, I reached the financial independence status, if you will. And so that class movement in the United States, I think, has given me a perspective on the country where I can tell you about the divide. I can tell you about the pain that's in the divide. And I can tell you how I think it happened and then what we could potentially do to fix it.

• 15:00Elizabeth Day?

  Great answer. No notes.

• 15:04Elizabeth Day?

  One of the things I hear a lot from listeners is how tiring it can be when your mind just doesn't settle. And I can only imagine this feels even heavier with intrusive thoughts. It's that quiet sense of being worn down by something you never asked for and never wanted, but just can't seem to switch off. If you struggle with this, I want to tell you about NoCD, because it's a resource that genuinely helps people. NoCD provides specialized treatment for OCD. And what I appreciate about their approach is how human it feels. You're matched with a licensed therapist trained in ERP therapy. That's Exposure and Response Prevention. And over time, you learn skills that help your OCD symptoms become

• 15:46Elizabeth Day?

  manageable, so you can live more of the life you want to live. If you're struggling with OCD or unrelenting intrusive thoughts, NoCD can help. Book a free 15-minute call to get started at learn.nocd.com/fail. Let's get on to your failures. Your first failure is being fired from Goldman Sachs, as your neighbor put it, but fired from Goldman Sachs.

• 16:09Speaker 00

  Yeah.

• 16:09Elizabeth Day?

  So.

• 16:10Speaker 00

  It's not a law firm, by the way. It's actually a high-profile investment bank. I mean, Mrs. Kazenza, I mean, I don't know why, my mother, I mean, come on.

• 16:18Elizabeth Day?

  So you graduated from Harvard Law School. You never went into the law. You went straight into Goldman Sachs.

• 16:22Speaker 00

  I didn't. And so, I mean, I was, one of my failures, actually, which wasn't one of the big three that we're going to mention here, but I, I failed the bar exam after law school.

• 16:31Elizabeth Day?

  Like Kim Kardashian.

• 16:32Speaker 00

  Yeah, yeah. Well, like John F. Kennedy Jr. too. And remember, he failed it a few times. But I, I failed the bar because I was going to Goldman, and this is how arrogant and how smug I was. I had never failed anything. And I figured I didn't have to study for it. That test is actually designed for you have to study for it. And so I failed the bar coming out of law school, out of Harvard Law School, no less. And my, my mother was super upset about that. And so I went back and took it and passed it. Okay. To appease her, but also I think it was another big message in my mind. You got to be a finisher in life, you know? So even though I didn't practice law, I went on to pass the bar. So

• 17:12Speaker 00

  that was a minor failure. And that was due to smugness and arrogance, frankly. And it was a bad, bad ideas all around. But anyway, we're back. But getting fired from Goldman, this is like the, the best and the worst story. So I went to Goldman Sachs, Elizabeth, because it was the coolest job at the time. So just hear me out. I'm a 25-year-old insecure kid from not even the outer boroughs of New York. I'm from working class family on Long Island. I've gotten to Harvard Law School. So I got to prove to people that I'm the coolest. So how do you do that? Well, you got to get the coolest job. Okay. So what the coolest job was at that time was real estate investment banking, because the real

• 17:57Speaker 00

  estate industry was super hot and so was investment banking. So if you combine the two of those, that was the hottest job. It was the most coveted job from the Harvard Business School and from the Harvard Law School the year I graduated. So I was hell-bent on getting that job. And the problem with that was I absolutely sucked at that job. I was, I was ill-suited for it. I had to be trained. I mean, I was able to convince the people to hire me. And I always tell younger people that you got to pick a job in life that you really like, that you're driven by, that you have passion for. Don't pick a job where you're trying to impress your friends, or you're trying to grab onto

• 18:37Speaker 00

  some status or a totem of status, which is a false promise to yourself. So this is an important lesson in failure, because I had done everything right to get the most coveted job, except I was not interested in the job and I sucked at the job. Okay. So I'm hired and start my work on the 14th of August, 1989. And on February 1st, 1991, you could look it up, it was a Friday night. I remember it like it was yesterday. My boss sat me down in his apartment in Greenwich Village, invited me over for a beer. And I went over to his house, have a beer, and he fired me. And they were downsizing because of the Gulf War and they were in the beginning of a recession. And he said something to

• 19:22Speaker 00

  me, these were immortal words that are burnt into my brains. I'll share them with you. He goes, you know, you're a great guy. You're a very hard worker. You're a disciplined guy. You absolutely suck at this job. Okay. You're just, it's the wrong job for you. And so I'm firing you. I'm letting you go. And here's your $11,000 severance check. And we're going to give you one week and our career resources place to build a resume and make some phone calls and stuff like that, but you're fired.

• 19:53Speaker 00

  I don't know why, and I don't know how I did this at that moment. But I said to him, I said, Mike, can I use you as a reference? I said, it's gotta be hard for you to fire me. He had fired like 20 people that day. He looked exhausted and I think the last person he fired. It was eight o'clock at night. And I said, I just, you know, you said I had a good work ethic and stuff like that. If I'm in the right job, can I call you for a reference? And he said, okay, absolutely no problem. And he said, said as much. And so I went home and I was like, what am I gonna do? I'm 27. I went to Harvard Law School. I've been fired from Goldman Sachs after 18 months. What am I gonna do? I went to the bank. I got three rolls of quarters. Why did I do that?

• 20:37Speaker 00

  Remember, this is before cell phones. And it was 25 cents to make a pay phone call. And I got three rolls of quarters and I was living outside of New York City. I took the train back into the city. It's in Grand Central Station, Elizabeth, and I was pumping quarters into pay phones to call people. I had a stack of resumes that I had printed out and I was gonna go look for a job. And I got on the phone with somebody and he said to me, listen, there's a job at Goldman Sachs in the sales and trading area. They've had a couple of people leave recently. You should try to get that job. So, next phone call was to Mike Facitelli, the guy that fired me. I'm still very close friends with him, by the way.

• 21:22Speaker 00

  And I said, Michael, I said, there's a job on the 20. I was fired on the 10th floor. I said, there's a job on the 29th floor. I said, I think I'd be good at that job. He said, you know, I think you actually would be good at that job. He went up to see the partner in charge of that area. And then he called me and he said, okay, they're gonna interview you tomorrow at XYZ time. And I got rehired into Goldman. Okay, so I got fired on February 1st. On March 26th, I got rehired into Goldman. And then the Personnel Department called me and they were like, hey, you know, we're gonna mark you down as interdepartmental transfer. We're never gonna have to tell anybody you got fired. Can we get the $11,000 check back? I was like, actually, you can. Actually, I've already spent it.

• 22:07Speaker 00

  You know, I've spent it on some of my school debt. I bought some suits for these interviews. I said, yeah, you can't get the money back. I said, no problem. You know, you can tell everybody in the world that I got fired. I don't care. She was great, by the way. She marked me down as interdepartmental transfer anyway. She just retired from Goldman, actually. 40 years at Goldman. She was in the Personnel Department.

• 22:28Elizabeth Day?

  And you didn't burn bridges, which I think is a temptation sometimes if you feel...

• 22:33Speaker 00

  Oh, yeah. Well, the number one thing you do is you blame everybody else but yourself. And then in the process of blaming everybody else, you burn all the bridges. That was Mike Facitelli's fault I got fired, not me. I didn't do anything wrong. See what I mean?

• 22:45Elizabeth Day?

  Yeah.

• 22:46Speaker 00

  But I don't know what it was. It was either instinct. I hadn't thought it out as carefully as I have today, 30 years after my firing, 35 years after my firing. But I, I definitely would implore people that when bad things are happening to you, take a step back, take a deep breath, and get into a channel inside your brain, okay, that is the adult channel. Okay, there's almost like, you know, like a psychotherapist would say, a witness mind. The witness mind is when you step out of yourself and you're observing yourself as a third party and then start acting in a very rational way. Don't let your emotions run the program for you.

• 23:29Elizabeth Day?

  What's your darkest characteristic?

• 23:33Speaker 00

  Well, I'm Italian. I mean, so I mean, you know what Italian Alzheimer's is?

• 23:40Elizabeth Day?

  No.

• 23:40Speaker 00

  We forget everything but the grudges. I mean, you know, we could be very vindictive and very vengeful. You know? You know what I'm talking about?

• 23:46Elizabeth Day?

  Yeah, I love, yes.

• 23:47Speaker 00

  Come on, you've seen enough Godfather movies. We get super wickedly pissed, right? You know? First of all, you have to understand those instincts and then you have to hit the override switch.

• 23:57Elizabeth Day?

  Hmm.

• 23:58Speaker 00

  Okay? And so you asked me something about being a pessimist. So I am an optimist today. I mean, I've trained my brain to be optimistic. I didn't start that way anymore than I started without having, you know, that like vengeance or anger-based vendetta and all that sort of stuff. You gotta, I'm not saying it doesn't exist, but you have to like do something transformational to overcome that and to make your responses at a higher human level. You know, that's, that's lower level thinking for a human being. Higher level thinking is the process of forgiveness, forgiveness of others, forgiving yourself

• 24:39Speaker 00

  and pushing yourself into a more sublime position as a human being. You're capable of doing it.

• 24:47Elizabeth Day?

  Wall Street in the late 80s, early 90s. What was it like?

• 24:51Speaker 00

  Lots of drugs, lots of drugs.

• 24:53Elizabeth Day?

  Okay. Did you partake?

• 24:55Speaker 00

  I actually didn't, by the way. This, and thank God I didn't because I come from like a family of drug addicts and alcoholics. And so I'm, you know, again, gambling addicts, drug addicts and alcoholics. So I made a decision at a very early age to avoid all of that stuff because I wanted to move from where I was. I looked at my family situation and I said, okay, if I do what every single person in this family is doing, I'm gonna end up like every single person in this family. So I gotta, I gotta switch it up. I've gotta think about it creatively and think about it alternatively. So I actually didn't do it. But when you say 80s on Wall Street, and I got there in the late 80s, early 90s, I'm thinking cocaine and booze. But go ahead. Sorry.

• 25:40Elizabeth Day?

  No, I'm fascinated because one of my favorite novels of all time is Tom Wolfe's The Bonfire of the Vanities.

• 25:45Speaker 00

  The Bonfire of the Vanities, yeah, it's very well written. Sherman McCoy.

• 25:47Elizabeth Day?

  Yes.

• 25:48Speaker 00

  Yeah.

• 25:49Elizabeth Day?

  Is it accurate?

• 25:49Speaker 00

  Anti-hero. Well, I would say, like The Godfather, art imitates life and life imitates art. And so like the mobsters watched The Godfather, then they became like the mobsters in The Godfather who were observing the mobsters who weren't in The Godfather to create the mobsters. I mean, I just said like a weird syllogism, but you get the point that I'm making. And so after, after The Bonfire of the Vanities came out, it became like an anti-hero novel, but people started to adopt the suspenders and the mannerisms of the people inside the, inside the book. You know, the social x-rays and the people getting super thin and all the different

• 26:33Speaker 00

  things started happening. Moreover, when Oliver Stone wrote and produced Wall Street, which was late, late 80s, I think Bonfire of the Vanities was like 86 or 87. Oliver's movie came out in December of 87. The anti-hero Gordon Gekko, Michael Douglas. I, I was in Wall Street 2.

• 26:52Elizabeth Day?

  I know.

• 26:53Speaker 00

  I had a, I had a role in Wall Street 2. I got close to Michael Douglas and Josh Brolin and Shia LaBeouf. And Michael told me that Wall Streeters would come up to him in New York City restaurants and say, hey, you know, it's because of you I came to Wall Street. And Michael would be thinking to himself, you know, I was like the insider trader bad guy that went to jail. Did you not remember that part of the movie? You know what I mean?

• 27:14Elizabeth Day?

  Lunches for wimps, famous line from Wall Street.

• 27:17Speaker 00

  Lunches for wimps, all of the stuff that he said in that movie.

• 27:22Elizabeth Day?

  Before we get on to your second failure, you have gone on to be incredibly successful in finance. Is it nice having lots of money?

• 27:31Speaker 00

  It's very nice to have money. There's no question about it. It's better than not having money, but like also with money does come some level of responsibility. So, again, I'm from a blue collar neighborhood, so I have family members that are not doing well. Okay, so if I have a family member that's been disabled because of hard labor, well, I guess what I'm doing is I'm subsidizing their life. So I want them to be okay. You know, I've paid for cars, health insurance, college tuition, master's degrees, you know, because these are people that I grew up with. You know, my, my mentor is a guy named Bob Cachergnano, and I acknowledge him in the book. And you may remember Ken Langone.

• 28:13Speaker 00

  I don't know if you would recognize the name, but if you're in New York, Kenny gave $200 million to NYU. It's now called the Langone Medical Center. And then he gave like $2 billion to the endowment so that if you get into medical school there, you can go for free. So he's one of my elder statesmen mentors. He just turned 90 last year. Those two guys would say to me, and they would say to you, Elizabeth, hey, man, if you've made it from a blue collar neighborhood and a blue collar family, help the people. Okay? And remember, the country does better when we put a hand out to reach up to somebody and pull them up. You follow what I'm saying?

• 28:52Elizabeth Day?

  Yeah.

• 28:52Speaker 00

  And so when you say, is it nice to have money? It is very nice to have money. I mean, I have like modest houses, but I do have houses. I don't have one house because I don't wanna live in this gigantic house because I think there's a paradox to wealth and I'm happy to explain that to you if you want my theory on it. But I love cars. You know, because my uncle was, I grew up in a motorcycle shop and so we always had cars around. And so when I was a kid manifesting my life, I'm like, okay, if I ever get rich enough, I'm gonna own a Rolls. I'm gonna own a Lambo. I mean, I'm a little bit of a nouveau riche Italian. What the hell you want from me? I mean, that's what it is, right? So, but I don't live in these big fancy pants houses because I think it's really bad for my kids. I want my kids to be able to cross the street, ring the doorbell next door and go play with

• 29:36Speaker 00

  the other kids in a neighborhood. There's a paradox to the wealth. So if you become very wealthy and then you gotta show off your wealth, what are you gonna do? You're gonna buy a big mansion. Okay, that's great. Now you got a 15 acre estate. Oh, that's great. Now your kids are sitting alone in the mansion. Oh, wait a minute, I'm super wealthy. Let me go fly around privately. Okay, now the kids don't see you in the airport. Oh, I go on the Disney Cruise. You know, Catty thinks I'm crazy. She hates Disney. But I go on the, my kids are socialized with these other kids on the Disney Cruise. See what I mean?

• 30:06Elizabeth Day?

  Yeah.

• 30:07Speaker 00

  If you're not careful, your wealth will make you very depressed and very lonely. It's almost like a, it's almost like a, it's like a sociological trap. I don't know. Maybe it's God or the universe playing a trick on you. Okay, you wanted to get the wealth and then the wealth becomes a Faustian bargain with the society if you're not careful with it. So I try to use my money for charity and help people. I do have a couple of nice things. I'm not gonna say that I don't because I do and I like nice things. And it's convenient from, to have access to medical care and things like that. But I'm trying to help the people around me with it.

• 30:43Elizabeth Day?

  No more Nissan cars.

• 30:45Speaker 00

  Oh, no more Nissan. Oh, yeah.

• 30:46Elizabeth Day?

  Nissan, sorry, Nissan. We had a linguistic.

• 30:49Speaker 00

  Yeah, I'm sorry. Yeah, we're separated by the common language.

• 30:55Elizabeth Day?

  There are so many things I wish I'd known when I started this podcast and my production company, Daylight. Like, why am I spending hours trying to make a website look good? Why am I designing everything from scratch? And why am I spending all my time just doing admin? What I really needed was one place that could do all of this for me. Enter Shopify. Shopify has beautiful, ready-made templates that make your website look polished without needing to become a graphic designer overnight. Its AI tools can help you get your site up and running quickly, and Shopify Checkout makes it really easy for customers to actually go from, ooh, I like that, to, yes, I'll have one. If Shopify had existed when I started out, I could have saved myself a lot of time, stress, and

• 31:40Elizabeth Day?

  some rogue design choices. If you're ready to hear the

• 31:45Elizabeth Day?

  of your first sale today, head over to Shopify.co.uk/fail to start your free trial today. That's right, start your free trial at Shopify.co.uk/fail. Your second failure is your first marriage.

• 32:01Speaker 00

  Yeah. And my ex-wife would probably be mad at me for talking about it so publicly, but I did all the wrong things in my marriage, actually. And, you know, like, this book is called All the Wrong Moves. If I was going to write a book about my shortcomings or my failures, it would have been a phone book. My first wife and I got married at 24, that was me, and she was 25, respectfully. We met in college. And we had a very good relationship in the beginning, but some of the problems that I had as a kid, I brought into my marriage. And so what were those problems? Well, my dad was a very strict disciplinarian. I mean, he used to beat the daylights out of us. And he was a temperamental guy. And so you

• 32:46Speaker 00

  can replicate that, right? Psychologically, you can downward shift into that, and you can become that, okay, which often does happen in situations where there's alcohol and there's other things going on in the family. Or you can try not to do that, right? And so, but what you got to be very careful of is you create this antipodal effect where you go to the other extreme. Okay, so here's the self-narration. Okay, ready?

• 33:13Elizabeth Day?

  Yes.

• 33:14Speaker 00

  I was in a pretty abusive, domestic situation as a kid. So therefore, I am not going to be abusive, and therefore, I'm going to be a conflict avoider. And so therefore, you and I are in a relationship, and you're doing things that I don't like, I'm not going to tell you about them. Because I fear conflict so much, that I'm not going to be able to express to you what the things are that are going on that are wrong in the relationship for me.

• 33:42Elizabeth Day?

  Yes.

• 33:43Speaker 00

  Does that make sense?

• 33:44Elizabeth Day?

  It makes so much sense. I relate.

• 33:46Speaker 00

  Okay. And so then, what happens is, you have this crazy job. So you've mentioned the money. But you have to remember, the money for me came with ridiculous amounts of work, and it came with W2 income. So what does that mean? Let's say if I made a million dollars, I live in the city and state of New York, I'm getting taxed 52% of it. I get to keep 48% of the money. And so you have to work off of the 48% of the money in each year in succession. And so I was working around the clock when I started my own business, where, which is, it's better if you can be successful in your own business in the United States, you'll make more money. But think about all the problems that you

• 34:28Speaker 00

  have in your business. And so now, was I neglectful to my marriage in that process? I 100% was. And it cost intimacy, it cost relatability, and then the, and then the conflict-avoiding, which was a terrible part of my personality. And I would recommend to people, if you're in a problem situation in your marriage, or things are not going right, you have to face the music with yourself first to figure out what it is, right? It's never 100-0. I mean, people can pretend, you know, we got divorced, she was 100% wrong,

• 35:09Speaker 00

  and I was 100% right, and it was 100-0. We can pretend that, but it's never that. You know, there's culpability on both sides. And so I didn't face those demons in my personality, and I didn't face, how can I say this? The, you know, you're, you have your nature, you're born a certain way, you're born a certain way, I'm born a certain way, but then you have your nurture, and that's affecting your personality, it's affecting the operating system of how you think. And I was so concerned about conflict, and the way I was treated as a kid, that I was never going to do that to anybody. But then that puts you too far

• 35:51Speaker 00

  away from the base standard of what is appropriate to say. You know, Elizabeth, we have a relationship, here's things that are going right in it, here's the things that are going wrong in it for me. And by the way, you may have some things like that, too. We love each other, let's try to figure it out. I didn't do that. And so that is a big epic fail on my part. And I don't have anybody to blame, other than myself. Our marriage ended up fizzling probably a decade before it actually ended. And we were both Roman Catholics, so we didn't get a divorce right away, because something about the church, you know, we tried to stay married, even though your marriage isn't working. Someone will have to explain that one to me in a different life, but then the Catholic, you know, the sacrament of marriage.

• 36:34Speaker 00

  But we, we were better off apart than we were together. But the way we ended it is something I really regret, because I didn't have the fortitude to handle it as directly as I am right now. But by the way, I will also say this, my second marriage almost ended in divorce as a result of my White House career, we'll get to that one. But I think the learning, the self-learning, and the self-edification of what went wrong in my first marriage helped me resolve whatever things that were going wrong on my second marriage. You're married once?

• 37:06Elizabeth Day?

  Twice.

• 37:07Speaker 00

  Twice. You're married right now?

• 37:09Elizabeth Day?

  Yes.

• 37:09Speaker 00

  Okay.

• 37:10Elizabeth Day?

  Going back to the conflict avoidance, which is something I hugely relate to.

• 37:15Speaker 00

  Yeah.

• 37:15Elizabeth Day?

  And it definitely had a part to play in the failure of my first marriage, although it wasn't the entire part. But the part of the reason I was conflict-avoidant is because I was scared. I was scared that if I stated something that I was, that was making me unhappy, that it would elicit a degree of anger, whether that fear was logical or rational or not, or whether it was inherited.

• 37:35Speaker 00

  How old were you when you got married the first time?

• 37:37Elizabeth Day?

  32. But we met when I was 29.

• 37:40Speaker 00

  Okay.

• 37:41Elizabeth Day?

  And I don't think, partly because of the conflict avoidance, I became a people-pleaser, and I don't think I'd done the work on myself that I thought I had. And I was just trying to keep people happy. And then I lost myself entirely. It's difficult, as a conflict-avoidant people-pleaser, to end a relationship, particularly a marriage. How did you end yours?

• 38:00Speaker 00

  Foolishly, you know, very badly. You know, I ended up having an affair, and the affair got exposed. And then there was probably some parental alienation, which I was upset about at the time, but I understand it better now from my ex-wife's perspective. That's my fault. I have to own that. You know, that was, that was not the right way to end a marriage. You know, I should have ended it differently. But I'm a human being, and by the way, a lot of marriages end that way. So then that's where the process has to begin, where you have to actually forgive yourself. That is a, a pain point for me, because you

• 38:40Speaker 00

  also have, at younger stages of your life, or at least I'll speak for myself, I had a hard time with the self-awareness. Like, the bad stuff that lurks in my personality that you've asked me to express, I was less willing to express that, right? I wanted to express only goody-two-shoes, and only a good guy, got my temper in check, not a con, you know, I'm a conflict-avoider, people-pleaser, but I'm a good guy, I want to show you my good side, none of my bad side. You see what I mean?

• 39:13Elizabeth Day?

  I do.

• 39:14Speaker 00

  And that, that is immaturity. And that's also a lack of self-awareness. Okay, so the reason why we're relating to each other, and you express this in your writing, is you could not write about these characters if you yourself didn't have really good self-awareness. Okay? And so you've developed that, and you probably didn't have that at 29, when you got married, or when you met the person, got married at 32, you probably didn't have it. But you were willing to make yourself have it. And I think that's the message to your viewers and listeners. You have to force yourself out of the comfort box of whatever your insecurities are, that will keep you in your little comfort box. You've got to break out of that.

• 39:54Elizabeth Day?

  Yes.

• 39:55Speaker 00

  You have to force yourself to feel the self-consciousness, the anxiety, the, you have to, like, all of a sudden have the awakening, wait a minute, I just did something really stupid or really flawed, and I did something that I always tell myself I would never do. I've acted in an immoral way when I'm trying to project pristine morality in the situation. Do you see what I'm saying?

• 40:20Elizabeth Day?

  So well put.

• 40:21Speaker 00

  Yeah, it's very hard to do.

• 40:22Elizabeth Day?

  Very hard.

• 40:22Speaker 00

  You have to do it. You have to do it, because if you don't do it, then you're not going to grow to be the person that you really could be.

• 40:27Elizabeth Day?

  And I think you also have to take the risk that you will be loved with all of your imperfections. Because so often, when we're projecting that idea of perfection, as you say, we're hiding or suppressing our shadow sides. And actually, real love, real belonging is acceptance of those aspects. You had three kids together, and you were married for over 20 years. So in many respects, it's such a successful relationship, even though it ended. How are you as a father?

• 41:00Speaker 00

  I mean, you would have to ask my kids. I think the divorce was very bruising and very traumatizing to my kids. And I think if my kids were sitting on this couch, hopefully, they would be sitting up properly. But if they were sitting on this couch, they would say to you that I hurt them very badly through the divorce process and through my actions. If I had been more of a straight up person and less of a conflict avoider, there probably would have been less pain in that divorce. I would also say to people that if they're listening and if going through something like this, because one of my friends recently went through a divorce. And I said, listen, there's no such thing with children as quality time.

• 41:45Speaker 00

  There's only quantity time. You got to spend as much time as humanly possible with your children. And the other thing I would say to you is that if you're trying and you have good intention, even if you've made mistakes as a father, which I have certainly made my share of mistakes, you'll win back your children, you know, because they'll come to you for guidance and they'll come to you. And also, as they get older, you become more human to them, right? You know, they idolize you when they're young, Elizabeth. They demonize you as they get to a certain age, and then they humanize you. Like, holy shit, my father's like me. You know, he's just an older version of me and he's going through this life and he's made his mistakes.

• 42:25Speaker 00

  And, you know, I can't really demonize him because he's, you know, he's human. Am I a good father? I'd like to think my kids would think I'm a good father. I would say that I'm a flawed father. I think they would definitely say, man, this guy's a really good provider. He's helped us out. He's paid for our educations. He's got us going in career tracks that we all love. He's made sure that our housing and all this different stuff has been secured for us. And I would say something about my children, which I adore about them. The mandate from them and from their mother, by the way, the mandate from me and their mother was do something you really like. I got enough money to help you out, so just do whatever you like. I've got one kid that went to Stanford Business School. He's in venture capital. My daughter is a singer.

• 43:07Speaker 00

  She was in concert with Andrea Bocelli last week, which I'm very proud of her. I was in Italy to go, and she has a great relationship with Veronica and Andrea. And she's been, she played Christine for Andrew Lloyd Webber in Phantom. She did a tour for them in 2023. She's been at the Tokyo Opera. She's got a great singing voice and she wants to be a singer. And so, God bless. And my 27 year old adult child is a young aspiring film director. He just, his short film won the Dublin Film Festival last year and the Tokyo Film Festival. So they're doing things differently than me, but they're doing things that they like, and I admire that in them.

• 43:47Elizabeth Day?

  Your third failure is your firing from the White House.

• 43:51Speaker 00

  Yeah, that was a big one.

• 43:52Elizabeth Day?

  Different kind of marriage. Tell us this story.

• 43:58Speaker 00

  Well, I mean, I think the biggest failure, the biggest, biggest failure of my life was the decision to go work for Donald Trump. And so there were so many things flawed about that decision. There were so many superficial things that I did upon hindsight and reflection to make that decision. But, or none. Now, would I know Elizabeth Day if I had not gone to work for Donald Trump? Probably not.

• 44:20Elizabeth Day?

  That's the biggest success story.

• 44:22Speaker 00

  Yeah, there you go. You see that, girl, right? So here I am. So the whole thing was worth it, you know? Now that I'm working for him in that environment, and one of my mentors told me not to do it. He told me that you and Trump are completely different people. It's one thing to work for him and volunteer for him on the campaign. You're a lifelong Republican and blah, blah, but you should step away from him. Jeb Bush, who I was very close to, who I'd worked for before he left the race, and then I ended up joining Trump's campaign, don't do it, told me not to do it. And so I didn't do that. And so this is a story of ego. And this is a story of pride, more than it's a story of anything else.

• 45:05Speaker 00

  And so if you grow up in a blue collar neighborhood like me, you go to Tufts and Harvard, you work at Goldman, you build two successful hedge funds, you now have the opportunity to go work for the American president.

• 45:18Speaker 00

  Okay? And in your mind, because you're so self-centered, you think you're going to help everybody by doing that, particularly the people that you grew up with. And so my wife really despised him.

• 45:30Elizabeth Day?

  This is your second wife, Deirdre?

• 45:31Speaker 00

  My second wife, my second wife, yep. She despised him. She knew stuff about him from her friends in the New York social community. And she was like, you can't go work for him, you know? I mean, she really despises him. I mean, I always tease and say that she hates him almost as much as Melania hates him, because that's like the, actually, I think I found one person that hates Trump more than Melania. That's like Mark Milley. General Milley hates Trump more than Melania, other than that, you know? So now, Deirdre and I got in a bone of contention related to that, which we can talk about, because it's part of the story. But I ignored all that. So I was going to put a round peg in a square hole.

• 46:13Speaker 00

  I'm going to go work for the President of the United States, because he's the President of the United States. And I'm going to go do that because it's ego-based, significance-based, all the stupid things that you would expect yourself not to do. And, you know, I read the Iliad, I read the Odyssey. I watched Matt Damon tie himself to the mast this summer as the sirens were screaming and, you know, seducing the sailors off the boat into the Caribbe's, into the whirlpool. And I said, my God, there it is. It's right there from 3,000 years ago, Homer telling us about ourselves. Homer telling us about how we can be tempted by certain things.

• 46:56Speaker 00

  And if we don't manage our pride and we don't manage our ego, it can force us into our own odyssey, right? It can force us into our own displacement. Despite reading it, Elizabeth, and despite thinking I was a know-it-all, I had to live it. I couldn't just read it and learn from it. I have to actually go and live it. So I went to go work for Donald Trump. I spent 11 faithful days in that administration. And I write about it in the book, The Real Reason Why I Got Fired. I got a very nice note from somebody I sent that book to, who was a former cabinet member. And he wrote me a very nice note about like how honest the book was about what was going on at the time in the Trump administration. And there was a group of people inside the administration

• 47:39Speaker 00

  that were trying to contain the worst aspects of the president's nefarious nature, which you don't have people like that in Trump, too. But when I got there, there was like a whole commotion going on. And I was like, okay, how am I going to help this situation? How am I going to fix it? I don't think I've ever told anybody this story, but can I tell you a quick story?

• 48:00Elizabeth Day?

  Definitely, when you preface it like that.

• 48:02Speaker 00

  Yeah, I've never told anybody, sorry. So my first day on the job, Sean Spicer quits. I'm like, okay, that's great, because now we don't have to fire him. Like, my nickname for him was Liar Spice, like all the Spice Girls have a nickname. His was like Liar Spice, right? So we had to get rid of him. And then Sarah became the press secretary. That was my idea with Trump. And then Trump asked me to do the first press conference, so of course I did that. But I'm in the lobby of the West Wing and H R McMaster is the National Security Advisor. And we have a lot of friends in common. And I had traveled to Afghanistan and Iraq on troop support missions with some of his other colleagues who were generals. And so now he brings me into his office, we have this long conversation, and he's getting me up to speed on some national security.

• 48:45Speaker 00

  I had gotten my clearance, and so we're, he's reading me into different things. And he says to me, listen, we're going to have a welcome to the West Wing party for you at my house. Okay, we're going to go to Fort Meade, so overlooking the Jefferson Memorial. We're going to have this like awesome party for you, and I'm going to invite all the people from the West Wing. I said, okay, Gary, I said, what do you want to do that? He says, August 1st. I said, August 1st it is. I'm like, I got my ass fired on July 31st, okay? So now McMaster, that callous bastard, he says to me, holy shit, you got fired. What am I going to do with the hot dogs and the keg of beer? I said, H R, we're going to have a farewell.

• 49:22Elizabeth Day?

  Yes.

• 49:23Speaker 00

  We're going to have a farewell party, okay? And I showed up at his house on August 1st and Gary Cohen and Mnuchin, all my buds from the administration, showed up and we cooked hot dogs and drank beer overlooking the Jefferson Memorial. So what are you going to do? Are you going to be a baby? Okay, I got my ass fired. We're not canceling the party. We just turned it into a farewell from the White House party.

• 49:44Elizabeth Day?

  And you write in the book, it's so fascinating, because you write about mistakes that you made. If you'd wanted to hold on to your job, you would have lied to the president, essentially. One of the quote unquote mistakes was that you were too honest with him or that you embarrassed him in front of other people, because you were telling him the truth.

• 50:04Speaker 00

  Yeah, well, it had to do with the Russian sanctions bill. For some reason, he's jacked up about Vladimir Putin. And so the House and the Senate had passed a sanctions bill related to election interference. This was July of 2017, and the president did not want to sign the bill. We had a conversation about it, and unfortunately, there were other people there. This was my mistake, actually. When I got fired, just another thing, I never blamed anybody else about my firing. I got fired, I did, you serve at the leisure of the President of the United States. If you're not doing the job that he wants you to do, he has the right to fire you. Don't be a baby about it. And so I'm fully accountable for my firing.

• 50:46Speaker 00

  But I said something to him that got him pissed off, which I said that they can veto the bill. And he didn't really, he's like, I'm the President of the United States. They can't veto the bill. And well, first of all, that's eighth grade social studies, okay? But second of all, that's how it works. I said, they're going to embarrass you. They're going to go to Schumer, get the 17 votes they need to overturn the bill. And he told Jared I embarrassed him. He told Jared I embarrassed him in front of other people. I told him something that I should have told him in private. He doesn't like, you know, he did this to other people. Like, you can't tell the president, you can't tell somebody like Trump the difference between a Shia and a Sunni. Number one, he doesn't know the difference, but he doesn't want other people to know that he doesn't know the difference.

• 51:30Speaker 00

  It doesn't want you, like, he'll think, he's got to put on his bully game to intimidate you, okay? Like, oh, you think you're a big shot, that you know something that I don't know? You follow what I'm saying? So he'll always go to intimidation and dress down somebody.

• 51:46Elizabeth Day?

  Jared, who you mentioned there, is Jared Kushner, his son-in-law. I mean, I don't want to dishonor the reputation of your father, but you were talking to me about growing up in a conflict-ridden household. Were there aspects of Trump that reminded you of that?

• 51:59Speaker 00

  My dad did and everything, you can, we can talk about. It's not a bad, really dishonor. Who the hell knows what happened to him when he was a kid?

• 52:04Elizabeth Day?

  Yeah. But Trump's bullying, did that take you back?

• 52:08Speaker 00

  So funny you say that. And, you know, he had elements of that type of style and that type of personality, but I was better prepared for that. I think I had done a lot of work on myself. Like, I just got done talking about my marriage and the failure of my marriage. I was way less of a conflict avoider at age 53 than I was at 23. I remember I got fired nine years ago. I'm 62 now. I was 53. So I was more ready for Trump. What took me off my game with him is the relationship I had with him during the campaign versus how it was in the White House. So, again, people can be mad at me for working for him. Some New Yorker said, well, he was always an asshole, and so you should have known

• 52:53Speaker 00

  he was an asshole. All that stuff aside, I had a pretty good rapport with him. I'm gonna tell you that I was his friend, because if you think you're Donald Trump's friend, you really have no self-awareness, because he's a transactional person. You're not his friend. The minute he thinks he doesn't need you, he'll run you over with the car. You know, he's like a Tony Soprano that way. So with me and him, we had a very good rapport. And one of his family members said to me that I reminded him of his dad, Fred Trump, in the sense that I made my own money. And I really, you're allowed to curse on this podcast?

• 53:25Elizabeth Day?

  Yes.

• 53:26Speaker 00

  Yeah, okay. So I basically, I didn't give a shit. Right? So he, he always said to his family members, I call Anthony because he gives it to me straight. He'd get on the phone. That's a stupid idea. But why is that a stupid idea? And I would tell him. So now I'm in the White House, and I was acting in that same way. He did not want that. He's the President of the United States, and he wanted everybody kowtowing to him and everybody deeply subservient to him. You know, there was a very, really funny story. If you ever invite Paul Ryan on your podcast, I was with Christine Lagarde, I think she's the ECU. We're in Davos. I told this story. I said, Paul, he's the former Speaker of the

• 54:07Speaker 00

  House. I said, Paul, I'm gonna tell Christine Lagarde this story, and you tell her if it's true or not. And he says, okay, go ahead. I said, well, we're at lunch with President Trump. And this happened on Tuesday. Elizabeth, I know, because I was only there for one Tuesday, so I know it was a Tuesday. We're having lunch together. And Trump is in an argument with Ryan, and he starts pushing his chest, saying, you work for me. You work for me. And Paul Ryan looks at him and goes, I don't work for you. I'm, I'm in a totally separate article of the Constitution. I mean, like, Trump didn't even understand the checks and balances in the Constitution, right? And Paul's like, yeah, well, that totally happened. So, so you have to understand, it's now that Friday, and I'm telling him

• 54:49Speaker 00

  that, and he didn't want to hear it. And then he said, I embarrassed him. And then I was told if I make it to Monday, I didn't get fired for the interview. To really understand Trump.

• 55:00Elizabeth Day?

  This is an interview you gave to the New Yorker?

• 55:01Speaker 00

  Yeah, yeah, yeah. It was really some funny shit in that interview. I said that Steve Bannon was committing auto fellatio in his office, although I said a little bit more graphically than that. But it was really fucking funny, right? No one gives a shit.

• 55:11Elizabeth Day?

  Just quickly, do you still bear a grudge against that journalist? Because he's a fellow Italian.

• 55:16Speaker 00

  So, a grudge, I don't bear a grudge. And I never mention his name for a number of different reasons, but I don't bear a grudge. Like, I have no feelings for him one way or another. It's sort of, I'm for apathy towards him. But I thought he was a really bad guy. Okay, so it's okay to forgive him and move on, and to forgive myself for having that conversation with him. But another thing for your viewers and listeners, if you've got bad people around you, jettison those people. Okay, you don't, they don't deserve your time. They don't deserve your energy. They don't deserve your positivity. If there are bad people around, jettison those people. Build boundaries. It's totally acceptable to you. You don't have to be a people pleaser, as you were talking about.

• 55:59Speaker 00

  You build the people around you, the portfolio of people that are gonna lift you. Right? And I tell my kids, you're the weighted average of the five people that you hang out with the most. So cut it out. So I don't talk about him. I never mention his name. But I have no grudge against him. I'm sort of apathetic to him. And so that's a good sign. Because, you know, a 20-year-old version of me, you know, from 40 years ago, or even a 30-year-old version of me, probably would have. Would have probably been more vindictive.

• 56:27Elizabeth Day?

  You were saying you didn't get fired because of that interview. You got fired.

• 56:30Speaker 00

  Okay, look, if you know Trump's personality, he thought that shit was really funny. Okay, didn't get fired for that. I got fired because I said something to him in front of a group of people that he didn't know, and he thought I was trying to embarrass him. And he fired me. And that's fine. I mean, I, you know, General Kelly, actually, is the one that fired me, because Trump, talk about conflict avoiding, Trump hates conflict. And, you know, I mean, he's a total conflict avoider. He's a keyboard warrior. He'll call Gavin bad names, like Governor Newsom, on, you know, Twitter, but he does not, he does not go after Gavin face to face. He'll be super nice to him face to face.

• 57:09Elizabeth Day?

  I want to come back to Trump in a minute, which is not a sentence I've ever said before, but I do. I want to talk about your second marriage to Deirdre, and how she filed for divorce, literally, during this time.

• 57:20Speaker 00

  Yeah.

• 57:21Elizabeth Day?

  You missed the birth of your son because you were at some Boy Scouts convention in West Virginia, weren't you?

• 57:25Speaker 00

  I write about all of that.

• 57:26Elizabeth Day?

  Yes.

• 57:27Speaker 00

  Again, this is a very big message to your viewers and listeners, okay? Don't make your relationships in your life disposable. Like, if you really love somebody, and you talk about the unconditionality of loving somebody, like, you have to accept every, every part of the person's personality, the good, bad, and the ugly. We were having issues in our marriage. Most of them were related to me and my ambition. And some of them were related to priorities, related to me. And she's a very strong person. And she's like, hey, man, if this not, if this isn't what you want, let's get a divorce. Okay? And so she sent a message. She's got an Italian streak in her personality. She's, we can't go to, like, remediation or, like, marriage counseling. She's got to fire in

• 58:09Speaker 00

  the divorce decree right away. Okay, she serves me with divorce papers. And then I stupidly still go forward. She actually served me on July 7. And I go to the White House on July 21. So there's a lot of miscalculations in there. But now she's pregnant with James. And he's due on August 8. But maybe the stress of the whole thing, she's giving birth to him on the 24th of July, which is a Monday. And I am in West Virginia at the Boy Scouts event with Donald Trump. And he's giving this big speech, and I'm there. And he's like, I mean, if you remember, the speech was like a disaster. He was talking about all this kind of weird sexual innuendo and all this stupid shit. And, and me and Kelly

• 58:52Speaker 00

  and Conway are looking at each other, going, how are we gonna cover that? I mean, this is like a disaster. And then Deirdre gives birth to James. I'm not there. Okay? Now, you have adversaries in politics that are on the opposing team, like Labour and Tories. But then you have the internal strife of the people that want your job, or they want to annihilate you due to jealousies and all this other stuff, right? You're a fiction writer, so you know that the truth is stranger than fiction, right? So there's a group of people inside the White House hate my guts, like Rice, Priebus, and those guys. They want to get the information to the tabloids that I've missed the birth of my son. Okay? But that's what happens in Washington, right? You gotta know that, right? So I'm now trying

• 59:35Speaker 00

  to figure this out with Deirdre. Missed the birth of my son, a complete disaster. I say the White House firing is a big failure, but I want to include the whole thing, including missing the birth of my son. And so now, I've gotta figure that out. I still love Deirdre. I'd like to stay married. I'm pretty sure she still loves me. And we have two beautiful young kids. Let's see if we can work it out. But I'm working at the White House. And so I've got all of these things going at the same time. Then I get abruptly fired. Okay. So this is to your viewers and listeners. Guys, if you're ever having a bad day, and it's not cancer, let me take you through my day on the 31st of July, okay?

• 1:00:16Speaker 00

  I am fired from the White House. I have missed the birth of my son. My wife has filed for divorce on me. I am torched and excoriated by the late-night comedians. I mean, I'm, I mean, we've got animation going on. I'm Tony Soprano on the Potomac. I'm a Jersey Shore cast member. I mean, they were saying shit about me. Some of it was actually really funny. Okay, I think Bill Hader on Saturday Night Live called me human cocaine. I was, I mean, some of this shit was funny. Okay. And I'm going through the whole thing. I'm getting lit up by the cable news pundits. And now I'm out of my ass. And I've got to go back and try to figure out if I can fix my marriage, rebuild my business. And then I gotta face the music with the press in terms of who I am as a person. Because

• 1:01:00Speaker 00

  let me tell you something about politics. When they go after you, and they create that ad hominem attack, they create a two-dimensional caricature of you. Okay? Because if they want to discredit you, then they gotta get in people's minds who you are in a very negative way. Right? And so then you have the responsibility, if you choose to take it, to blow yourself back up. You gotta create three dimensions again. But this is where you are. Right? So that was my day on the 31st of July, 2017. So I went and repaired my marriage. We're, it's nine years later. We're still married. I think we're stronger

• 1:01:41Speaker 00

  than ever as a result of what we went through. I went and repaired my business. And then I made a decision. And even though I love Howard Bragman, he gave me bad advice. I always tease him about it, by the way. I faced the music with the late-night comedians, the cable news, and all the different people. And then I went and, you know, built a pretty good speaking portfolio in, in the United States, talking about these issues. And then Katie Kay came to me and said, hey, do you want to do this podcast? So that's a nine-year odyssey to me meeting Elizabeth Day.

• 1:02:16Elizabeth Day?

  Finally, finally.

• 1:02:19Speaker 00

  Is that real enough for you?

• 1:02:21Elizabeth Day?

  That's so real.

• 1:02:22Speaker 00

  It can't be realer than that, right?

• 1:02:24Elizabeth Day?

  No, it's everything I would ever want a guest to say. Thank you. You've seen Trump up close. You have this hugely successful podcast. You've written what is destined to be a best, another bestseller.

• 1:02:38Speaker 00

  I'm not gonna, let's hope.

• 1:02:40Elizabeth Day?

  And how scared are you about this particular inflection point in our global history in terms of what Trump could do next?

• 1:02:52Speaker 00

  I'm scared. I'm not going to say that I'm not scared, but I maybe I'm also very optimistic. I feel like Trump has exposed something so gnarly about aspects of the American body politic that there's enough smart people in the room, men and women, looking around saying, okay, well, we can't have this. We can't have a morally object, morally corrupt president running the largest economy with the most powerful military. So we're going to have to figure out a way to reform this. And so, so I believe that. And I believe that reform is coming. I don't like what the Democratic Party is doing. Like, I would tell you, and I've said this openly on the podcast, that the best thing that Trump has going for him

• 1:03:37Speaker 00

  are the Democrats. I mean, they feel the two poor candidates against them. When they feel that a benign, mediocre candidate against them, that benign, mediocre candidate beat them and beat them as a sitting president. So I'm worried about them because they're in disarray and they fight with each other. You know, Katty Kay has a great line, which I'll share with you. She says that Democrats fall in love and Republicans fall in line. So if Ted Cruz's supporter votes for him in the primary and he loses to Donald Trump, they vote for Donald Trump. Bernie Sanders's voters didn't vote for Hillary Clinton. You couldn't get the party consolidated around Kamala Harris. They either didn't show up

• 1:04:19Speaker 00

  in the polls, okay, or they tentatively voted for her. And that's just not enough support. You got to get the whole party. You got to get the coalition together the way Barack Obama did. See what I mean? And they're fighting with each other. The alt-left in that party is fighting with the centrists in the party. But I hope they win. Even though I'm a lifelong Republican, I hope they win because we need tremendous systemic reform.

• 1:04:45Elizabeth Day?

  Anthony Scaramucci, I could speak to you for days on end. I've loved this so, so much.

• 1:04:51Speaker 00

  It's been a pleasure for me to speak to you as well. You know, I'm a huge fan of yours. You're a brilliant writer.

• 1:04:57Elizabeth Day?

  Thank you.

• 1:04:57Speaker 00

  And you are also, you have the lantern on, Elizabeth. You're searching. You know, the podcast is great because you're really searching for people. And also, you want people to be able to express their fragility and their weaknesses in a way that in many ways strengthens them and makes them a better person. And it's very relatable.

• 1:05:20Elizabeth Day?

  Well, thank you for saying that. And thank you for being not only an epic failure, but an epic guest. Thank you so much for coming on How to Fail.

• 1:05:30Elizabeth Day?

  I hope you got as much out of this episode of How to Fail as I did. Brought to you by Ala Lacto Free. All the taste, easier to digest. Please do follow How to Fail to get new episodes as they land on Apple Podcasts, Spotify, Amazon Music, or wherever you get your podcasts. Please tell all your friends. This is an Elizabeth Day and Sony Music Entertainment original podcast. Thank you so much for listening.